Thionyl Chloride → Hydrochloric Acid

HRID 1609830Notes

Reaction equation

HRID 1609830 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([CH2:13]O)=[N:6][CH:7]=[C:8]([O:10][CH2:11][CH3:12])[CH:9]=1)[CH3:2].O=S(Cl)[Cl:17]>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:17][CH2:13][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:9][C:8]([O:10][CH2:11][CH3:12])=[CH:7][N:6]=1.[ClH:17]

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 22260398(3,5-Diethoxypyridin-2-yl)methanol

Product 2

HCID 313Hydrochloric AcidHCID 22260384HCID 22260384, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (3,5-diethoxy-pyridin-2-yl)-methanol (166 mg, 0.84 mmol) in CH2Cl2 (5 mL) is added 2.0 M solution of SOCl2 (1 mL) in CH2Cl2. The reaction mixture is stirred at room temperature for 30 minutes, diluted with toluene and concentrated to afford 2-chloromethyl-3,5-diethoxy-pyridine as HCl salt which is directly used for the next step.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-25eccd8f5f1a4b23a3875b044c898634
Source dataset
uspto-grants-2006_01
Patent number
US06982268B2

Reaction notes

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